Design and synthesis of a novel peptidomimetic inhibitor of HIV-1 Tat-TAR interactions: squaryldiamide as a new potential bioisostere of unsubstituted guanidine

Chi-Wan Lee; Hong Cao; Kozi Ichiyama; Tariq M Rana

doi:10.1016/j.bmcl.2005.06.077

Design and synthesis of a novel peptidomimetic inhibitor of HIV-1 Tat-TAR interactions: squaryldiamide as a new potential bioisostere of unsubstituted guanidine

Bioorg Med Chem Lett. 2005 Oct 1;15(19):4243-6. doi: 10.1016/j.bmcl.2005.06.077.

Authors

Chi-Wan Lee¹, Hong Cao, Kozi Ichiyama, Tariq M Rana

Affiliation

¹ Chemical Biology Program, Department of Biochemistry and Molecular Pharmacology, University of Massachusetts Medical School, Worcester, MA 01605-2324, USA.

PMID: 16054360
DOI: 10.1016/j.bmcl.2005.06.077

Abstract

By performing RNA-targeted structure-activity relationship studies, we discovered a novel peptidomimetic containing squaryldiamide as a potential bioisostere replacement for guanidine that binds transactivation responsive RNA with high affinity.

MeSH terms

Anti-HIV Agents / chemical synthesis*
Anti-HIV Agents / pharmacology
Cyclobutanes
Diamide / chemical synthesis*
Diamide / pharmacology
Drug Design
Gene Products, tat / chemistry*
Guanidine
HIV Long Terminal Repeat / drug effects*
HIV-1 / chemistry*
Molecular Mimicry
Oligopeptides / chemical synthesis*
Oligopeptides / metabolism
Oligopeptides / pharmacology
RNA-Binding Proteins / chemistry
Structure-Activity Relationship
tat Gene Products, Human Immunodeficiency Virus

Substances

Anti-HIV Agents
Cyclobutanes
Gene Products, tat
Oligopeptides
RNA-Binding Proteins
tat Gene Products, Human Immunodeficiency Virus
Diamide
Guanidine
squaric acid